N2-Isobutyryl-2'-O-methylguanosine
[CAS# 63264-29-9]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: N2-Isobutyryl-2'-O-methylguanosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• Molecular Formula: C₁₅H₂₁N₅O₆
• Molecular Weight: 367.36
• CAS Registry Number: 63264-29-9
• EC Number: 972-537-7
• SMILES: CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)OC

Properties

• Solubility: Very slightly soluble (0.55 g/L) (25 °C), Calc.^*
• Density: 1.68±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

N2-isobutyryl-2'-O-methylguanosine is an important nucleoside derivative with a place in nucleic acid chemistry and molecular biology. This compound features an isobutyryl group at the N2 position and a methyl group at the 2'-O position, which has unique properties that enhance its stability and functionality in a variety of applications.

The discovery of N2-isobutyryl-2'-O-methylguanosine stems from efforts to develop modified nucleosides with increased stability and functionality for synthetic and therapeutic applications. Researchers have sought to enhance the properties of guanosine by introducing protecting groups that provide greater stability, protection from enzymatic degradation, and increase the efficiency of nucleic acid synthesis. The combination of an isobutyryl group at the N2 position and a methyl group at the 2'-O position achieves these goals, resulting in a robust and versatile nucleoside derivative.

N2-isobutyryl-2'-O-methylguanosine is widely used in the synthesis of RNA molecules. These modifications enhance the stability of the RNA chain, making it more resistant to degradation by nucleases. This stability is essential for creating high-fidelity RNA sequences for a variety of research and therapeutic applications, including the development of mRNA vaccines and RNA-based drugs.

In the field of antiviral and anticancer research, N2-isobutyryl-2'-O-methylguanosine is a key building block for the design of nucleoside analogs. These analogs can inhibit viral replication or interfere with cancer cell proliferation by incorporating into nucleic acids and disrupting essential biological processes. The enhanced stability and specificity of these modified nucleosides make them promising candidates for the development of novel antiviral and anticancer therapeutics.

The compound is also valuable in chemical biology for studying nucleic acid interactions and function. The unique properties of N2-isobutyryl-2'-O-methylguanosine allow researchers to create stable RNA and DNA probes for studying molecular mechanisms and interactions within cells. These probes aid in the understanding of genetic regulation, RNA processing, and protein-nucleic acid interactions.

N2-isobutyryl-2'-O-methylguanosine is a key component in the design of therapeutic oligonucleotides, including antisense oligonucleotides and small interfering RNA (siRNA). These modifications enhance the stability and binding affinity of these oligonucleotides, improving their efficacy in targeting specific RNA sequences for gene silencing or regulation. This has important implications for treating genetic disorders and diseases caused by abnormal gene expression.

References

2008. Synthesis and biochemical application of 2'-O-methyl-3'-thioguanosine as a probe to explore group I intron catalysis. Bioorganic & Medicinal Chemistry, 16(10).
DOI: 2664738